# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_151214_yk_3_139
_database_code_depnum_ccdc_archive 'CCDC 1445009'
_audit_update_record             
;
2016-01-02 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;
_audit_creation_date             2015-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C30 H34 N2 O9'
_chemical_formula_sum            'C30 H34 N2 O9'
_chemical_formula_weight         566.59
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   9.09127(13)
_cell_length_b                   10.54359(15)
_cell_length_c                   30.6974(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2942.49(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9178
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3693
_cell_measurement_theta_min      4.1896
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19424
_diffrn_reflns_theta_full        67.48
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_min         4.43
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0152282000
_diffrn_orient_matrix_UB_12      -0.0499083000
_diffrn_orient_matrix_UB_13      -0.0469465000
_diffrn_orient_matrix_UB_21      0.1215284000
_diffrn_orient_matrix_UB_22      -0.0919631000
_diffrn_orient_matrix_UB_23      0.0149897000
_diffrn_orient_matrix_UB_31      -0.1171289000
_diffrn_orient_matrix_UB_32      -0.1019861000
_diffrn_orient_matrix_UB_33      0.0094638000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4859
_reflns_number_total             5252
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack (1983), 2238 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.05(13)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         5252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.2142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0803
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.57646(14) 0.84378(11) 0.13670(4) 0.0490(3) Uani 1 d . . .
O2 O 0.69692(12) 0.57138(10) -0.01382(3) 0.0385(2) Uani 1 d . . .
H2 H 0.7580 0.6138 -0.0270 0.058 Uiso 1 calc . . GR
O3 O 0.38839(13) 0.79691(10) 0.06423(4) 0.0455(3) Uani 1 d . . .
O4 O 0.60657(17) 0.24944(13) 0.00390(5) 0.0598(4) Uani 1 d . . .
O5 O 0.47868(14) 0.22868(10) 0.06569(4) 0.0469(3) Uani 1 d . . .
O6 O 0.72770(16) 0.40115(15) 0.16487(4) 0.0616(4) Uani 1 d . . .
O7 O 0.50001(13) 0.45927(13) 0.14190(3) 0.0466(3) Uani 1 d . . .
O8 O 0.82623(15) 0.20052(12) 0.09248(6) 0.0714(5) Uani 1 d . . .
O9 O 1.03997(12) 0.29894(11) 0.10513(4) 0.0450(3) Uani 1 d . . .
N1 N 0.54651(13) 0.63510(11) 0.07451(4) 0.0300(3) Uani 1 d . . .
N2 N 0.68542(13) 0.44547(11) 0.09411(4) 0.0322(3) Uani 1 d . . .
C1 C 0.68735(18) 0.81971(14) 0.10801(5) 0.0376(3) Uani 1 d . . .
C2 C 0.8190(2) 0.88544(16) 0.10632(6) 0.0482(4) Uani 1 d . . .
H2A H 0.8340 0.9540 0.1248 0.058 Uiso 1 calc . . R
C3 C 0.9291(2) 0.85041(17) 0.07736(6) 0.0481(4) Uani 1 d . . .
H3 H 1.0153 0.8978 0.0762 0.058 Uiso 1 calc . . R
C4 C 0.91364(18) 0.74684(15) 0.05016(5) 0.0389(3) Uani 1 d . . .
H4 H 0.9888 0.7223 0.0314 0.047 Uiso 1 calc . . R
C5 C 0.78204(16) 0.68106(13) 0.05189(5) 0.0322(3) Uani 1 d . . .
C6 C 0.66892(16) 0.71943(13) 0.07876(5) 0.0319(3) Uani 1 d . . .
C7 C 0.74170(15) 0.55679(14) 0.02973(5) 0.0308(3) Uani 1 d . . .
C8 C 0.60730(15) 0.51271(12) 0.05868(4) 0.0283(3) Uani 1 d . . .
C9 C 0.41082(16) 0.68215(14) 0.06380(5) 0.0343(3) Uani 1 d . . .
C10 C 0.29361(17) 0.58949(16) 0.05096(6) 0.0419(4) Uani 1 d . . .
H10A H 0.2641 0.6077 0.0212 0.050 Uiso 1 calc . . R
H10B H 0.2085 0.6034 0.0694 0.050 Uiso 1 calc . . R
C11 C 0.33572(17) 0.45103(15) 0.05377(5) 0.0371(3) Uani 1 d . . .
H11A H 0.2656 0.4000 0.0376 0.044 Uiso 1 calc . . R
H11B H 0.3344 0.4235 0.0839 0.044 Uiso 1 calc . . R
C12 C 0.48982(16) 0.43351(13) 0.03474(5) 0.0319(3) Uani 1 d . . .
H12 H 0.4864 0.4645 0.0047 0.038 Uiso 1 calc . . R
C13 C 0.84329(17) 0.42841(14) 0.08584(5) 0.0364(3) Uani 1 d . . .
H13 H 0.9004 0.4900 0.1027 0.044 Uiso 1 calc . . R
C14 C 0.85776(16) 0.45620(15) 0.03712(5) 0.0366(3) Uani 1 d . . .
H14A H 0.9551 0.4878 0.0301 0.044 Uiso 1 calc . . R
H14B H 0.8381 0.3810 0.0199 0.044 Uiso 1 calc . . R
C15 C 0.6082(3) 0.9278(2) 0.17192(7) 0.0698(6) Uani 1 d . . .
H15A H 0.6307 1.0105 0.1606 0.105 Uiso 1 calc . . GR
H15B H 0.6910 0.8962 0.1880 0.105 Uiso 1 calc . . GR
H15C H 0.5243 0.9332 0.1908 0.105 Uiso 1 calc . . GR
C16 C 0.53367(17) 0.29465(14) 0.03271(5) 0.0374(3) Uani 1 d . . .
C17 C 0.5146(2) 0.09507(16) 0.06811(7) 0.0584(5) Uani 1 d . . .
H17A H 0.4569 0.0491 0.0472 0.088 Uiso 1 calc . . GR
H17B H 0.4935 0.0641 0.0968 0.088 Uiso 1 calc . . GR
H17C H 0.6172 0.0834 0.0619 0.088 Uiso 1 calc . . GR
C18 C 0.64182(18) 0.43356(16) 0.13660(5) 0.0407(4) Uani 1 d . . .
C19 C 0.4326(2) 0.4592(2) 0.18573(6) 0.0580(5) Uani 1 d . . .
C20 C 0.5077(4) 0.5579(3) 0.21378(7) 0.0826(7) Uani 1 d . . .
H20A H 0.6060 0.5307 0.2203 0.124 Uiso 1 calc . . GR
H20B H 0.4537 0.5684 0.2404 0.124 Uiso 1 calc . . GR
H20C H 0.5111 0.6372 0.1984 0.124 Uiso 1 calc . . GR
C21 C 0.2758(3) 0.4972(3) 0.17575(8) 0.0873(8) Uani 1 d . . .
H21A H 0.2748 0.5801 0.1628 0.131 Uiso 1 calc . . GR
H21B H 0.2196 0.4984 0.2022 0.131 Uiso 1 calc . . GR
H21C H 0.2333 0.4372 0.1559 0.131 Uiso 1 calc . . GR
C22 C 0.4386(4) 0.3266(3) 0.20454(8) 0.0904(9) Uani 1 d . . .
H22A H 0.4022 0.2672 0.1835 0.136 Uiso 1 calc . . GR
H22B H 0.3791 0.3227 0.2303 0.136 Uiso 1 calc . . GR
H22C H 0.5385 0.3058 0.2118 0.136 Uiso 1 calc . . GR
C23 C 0.89637(18) 0.29510(15) 0.09534(6) 0.0430(4) Uani 1 d . . .
C24 C 1.1145(2) 0.17800(17) 0.10782(7) 0.0527(5) Uani 1 d . . .
H24A H 1.2176 0.1902 0.1008 0.063 Uiso 1 calc . . R
H24B H 1.0732 0.1213 0.0861 0.063 Uiso 1 calc . . R
C25 C 1.1032(2) 0.11627(18) 0.15166(7) 0.0553(5) Uani 1 d . . .
C26 C 1.0235(3) 0.1666(3) 0.18522(8) 0.0812(7) Uani 1 d . . .
H26 H 0.9720 0.2418 0.1810 0.097 Uiso 1 calc . . R
C27 C 1.0185(5) 0.1069(4) 0.22547(12) 0.1233(13) Uani 1 d . . .
H27 H 0.9648 0.1423 0.2482 0.148 Uiso 1 calc . . R
C28 C 1.0940(5) -0.0054(5) 0.23158(14) 0.1316(16) Uani 1 d . . .
H28 H 1.0910 -0.0462 0.2584 0.158 Uiso 1 calc . . R
C29 C 1.1733(4) -0.0567(3) 0.19787(15) 0.1131(12) Uani 1 d . . .
H29 H 1.2242 -0.1323 0.2020 0.136 Uiso 1 calc . . R
C30 C 1.1781(3) 0.0031(2) 0.15803(10) 0.0775(7) Uani 1 d . . .
H30 H 1.2317 -0.0324 0.1353 0.093 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.362(2) . ?
O1 C15 1.427(2) . ?
O2 H2 0.8200 . ?
O2 C7 1.4058(18) . ?
O3 C9 1.2271(19) . ?
O4 C16 1.204(2) . ?
O5 C16 1.326(2) . ?
O5 C17 1.448(2) . ?
O6 C18 1.216(2) . ?
O7 C18 1.327(2) . ?
O7 C19 1.479(2) . ?
O8 C23 1.187(2) . ?
O9 C23 1.340(2) . ?
O9 C24 1.446(2) . ?
N1 C6 1.4304(19) . ?
N1 C8 1.4855(18) . ?
N1 C9 1.3696(19) . ?
N2 C8 1.4797(18) . ?
N2 C13 1.469(2) . ?
N2 C18 1.369(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.397(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(2) . ?
C5 C6 1.379(2) . ?
C5 C7 1.521(2) . ?
C7 C8 1.581(2) . ?
C7 C14 1.513(2) . ?
C8 C12 1.542(2) . ?
C9 C10 1.498(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.512(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.529(2) . ?
C12 H12 0.9800 . ?
C12 C16 1.519(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.530(2) . ?
C13 C23 1.514(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 C20 1.513(3) . ?
C19 C21 1.512(4) . ?
C19 C22 1.514(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.498(3) . ?
C25 C26 1.367(4) . ?
C25 C30 1.387(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.387(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.381(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.373(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.377(4) . ?
C30 H30 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C15 117.10(15) . . ?
C7 O2 H2 109.5 . . ?
C16 O5 C17 117.67(15) . . ?
C18 O7 C19 120.94(14) . . ?
C23 O9 C24 116.26(13) . . ?
C6 N1 C8 106.29(11) . . ?
C9 N1 C6 119.83(11) . . ?
C9 N1 C8 124.83(12) . . ?
C13 N2 C8 113.62(11) . . ?
C18 N2 C8 127.24(12) . . ?
C18 N2 C13 115.88(12) . . ?
O1 C1 C2 124.81(14) . . ?
O1 C1 C6 117.88(14) . . ?
C2 C1 C6 117.29(15) . . ?
C1 C2 H2A 119.5 . . ?
C1 C2 C3 120.94(15) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.58(16) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.45(16) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C7 128.54(14) . . ?
C6 C5 C4 121.37(14) . . ?
C6 C5 C7 109.90(12) . . ?
C1 C6 N1 128.49(14) . . ?
C5 C6 N1 110.07(12) . . ?
C5 C6 C1 121.13(14) . . ?
O2 C7 C5 113.62(12) . . ?
O2 C7 C8 110.06(11) . . ?
O2 C7 C14 114.92(12) . . ?
C5 C7 C8 100.85(11) . . ?
C14 C7 C5 111.62(12) . . ?
C14 C7 C8 104.39(11) . . ?
N1 C8 C7 102.47(10) . . ?
N1 C8 C12 111.63(11) . . ?
N2 C8 N1 110.76(11) . . ?
N2 C8 C7 100.55(11) . . ?
N2 C8 C12 115.04(11) . . ?
C12 C8 C7 115.25(12) . . ?
O3 C9 N1 120.28(14) . . ?
O3 C9 C10 121.84(14) . . ?
N1 C9 C10 117.87(13) . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
C9 C10 C11 115.75(13) . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
C10 C11 C12 109.08(13) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C8 C12 H12 106.9 . . ?
C11 C12 C8 112.77(12) . . ?
C11 C12 H12 106.9 . . ?
C16 C12 C8 111.09(12) . . ?
C16 C12 C11 111.87(12) . . ?
C16 C12 H12 106.9 . . ?
N2 C13 H13 110.2 . . ?
N2 C13 C14 103.27(12) . . ?
N2 C13 C23 113.06(13) . . ?
C14 C13 H13 110.2 . . ?
C23 C13 H13 110.2 . . ?
C23 C13 C14 109.81(14) . . ?
C7 C14 C13 102.77(12) . . ?
C7 C14 H14A 111.2 . . ?
C7 C14 H14B 111.2 . . ?
C13 C14 H14A 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.1 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O5 124.11(15) . . ?
O4 C16 C12 123.81(15) . . ?
O5 C16 C12 112.05(13) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C18 O7 126.40(16) . . ?
O6 C18 N2 121.31(16) . . ?
O7 C18 N2 112.29(13) . . ?
O7 C19 C20 109.32(17) . . ?
O7 C19 C21 101.92(16) . . ?
O7 C19 C22 109.41(18) . . ?
C20 C19 C22 113.7(2) . . ?
C21 C19 C20 111.0(2) . . ?
C21 C19 C22 110.9(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O8 C23 O9 124.42(15) . . ?
O8 C23 C13 126.46(15) . . ?
O9 C23 C13 109.00(14) . . ?
O9 C24 H24A 108.8 . . ?
O9 C24 H24B 108.8 . . ?
O9 C24 C25 113.71(17) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C26 C25 C24 123.01(18) . . ?
C26 C25 C30 119.2(2) . . ?
C30 C25 C24 117.8(2) . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.6(4) . . ?
C28 C27 H27 120.2 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.8(3) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C25 C30 H30 119.9 . . ?
C29 C30 C25 120.2(3) . . ?
C29 C30 H30 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 176.80(16) . . . . ?
O1 C1 C6 N1 -0.3(2) . . . . ?
O1 C1 C6 C5 -173.22(14) . . . . ?
O2 C7 C8 N1 -92.13(13) . . . . ?
O2 C7 C8 N2 153.64(11) . . . . ?
O2 C7 C8 C12 29.32(16) . . . . ?
O2 C7 C14 C13 -160.28(12) . . . . ?
O3 C9 C10 C11 -177.61(15) . . . . ?
O9 C24 C25 C26 3.2(3) . . . . ?
O9 C24 C25 C30 -176.57(17) . . . . ?
N1 C8 C12 C11 -33.67(16) . . . . ?
N1 C8 C12 C16 -160.18(12) . . . . ?
N1 C9 C10 C11 3.5(2) . . . . ?
N2 C8 C12 C11 93.64(15) . . . . ?
N2 C8 C12 C16 -32.87(17) . . . . ?
N2 C13 C14 C7 33.44(14) . . . . ?
N2 C13 C23 O8 29.8(3) . . . . ?
N2 C13 C23 O9 -154.01(14) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
C2 C1 C6 N1 178.22(15) . . . . ?
C2 C1 C6 C5 5.3(2) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C3 C4 C5 C6 1.9(2) . . . . ?
C3 C4 C5 C7 -172.52(15) . . . . ?
C4 C5 C6 N1 -179.68(13) . . . . ?
C4 C5 C6 C1 -5.5(2) . . . . ?
C4 C5 C7 O2 -82.74(19) . . . . ?
C4 C5 C7 C8 159.55(15) . . . . ?
C4 C5 C7 C14 49.2(2) . . . . ?
C5 C7 C8 N1 28.16(13) . . . . ?
C5 C7 C8 N2 -86.07(12) . . . . ?
C5 C7 C8 C12 149.61(12) . . . . ?
C5 C7 C14 C13 68.46(15) . . . . ?
C6 N1 C8 N2 74.35(13) . . . . ?
C6 N1 C8 C7 -32.17(13) . . . . ?
C6 N1 C8 C12 -156.06(11) . . . . ?
C6 N1 C9 O3 -11.0(2) . . . . ?
C6 N1 C9 C10 167.97(13) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
C6 C5 C7 O2 102.36(14) . . . . ?
C6 C5 C7 C8 -15.35(15) . . . . ?
C6 C5 C7 C14 -125.73(14) . . . . ?
C7 C5 C6 N1 -4.35(16) . . . . ?
C7 C5 C6 C1 169.78(13) . . . . ?
C7 C8 C12 C11 -150.02(12) . . . . ?
C7 C8 C12 C16 83.48(15) . . . . ?
C8 N1 C6 C1 -149.65(15) . . . . ?
C8 N1 C6 C5 23.92(15) . . . . ?
C8 N1 C9 O3 -153.42(14) . . . . ?
C8 N1 C9 C10 25.5(2) . . . . ?
C8 N2 C13 C14 -15.08(15) . . . . ?
C8 N2 C13 C23 -133.69(14) . . . . ?
C8 N2 C18 O6 -163.61(16) . . . . ?
C8 N2 C18 O7 17.3(2) . . . . ?
C8 C7 C14 C13 -39.64(14) . . . . ?
C8 C12 C16 O4 -88.75(19) . . . . ?
C8 C12 C16 O5 93.06(15) . . . . ?
C9 N1 C6 C1 61.7(2) . . . . ?
C9 N1 C6 C5 -124.68(14) . . . . ?
C9 N1 C8 N2 -139.06(13) . . . . ?
C9 N1 C8 C7 114.42(14) . . . . ?
C9 N1 C8 C12 -9.47(18) . . . . ?
C9 C10 C11 C12 -43.8(2) . . . . ?
C10 C11 C12 C8 59.15(17) . . . . ?
C10 C11 C12 C16 -174.76(13) . . . . ?
C11 C12 C16 O4 144.25(16) . . . . ?
C11 C12 C16 O5 -33.94(18) . . . . ?
C13 N2 C8 N1 -116.66(13) . . . . ?
C13 N2 C8 C7 -8.87(14) . . . . ?
C13 N2 C8 C12 115.59(14) . . . . ?
C13 N2 C18 O6 -5.5(2) . . . . ?
C13 N2 C18 O7 175.42(13) . . . . ?
C14 C7 C8 N1 144.04(11) . . . . ?
C14 C7 C8 N2 29.81(14) . . . . ?
C14 C7 C8 C12 -94.51(14) . . . . ?
C14 C13 C23 O8 -85.0(2) . . . . ?
C14 C13 C23 O9 91.25(16) . . . . ?
C15 O1 C1 C2 -11.0(2) . . . . ?
C15 O1 C1 C6 167.32(16) . . . . ?
C17 O5 C16 O4 3.0(2) . . . . ?
C17 O5 C16 C12 -178.84(14) . . . . ?
C18 O7 C19 C20 60.5(3) . . . . ?
C18 O7 C19 C21 178.08(19) . . . . ?
C18 O7 C19 C22 -64.5(3) . . . . ?
C18 N2 C8 N1 41.90(19) . . . . ?
C18 N2 C8 C7 149.69(14) . . . . ?
C18 N2 C8 C12 -85.85(17) . . . . ?
C18 N2 C13 C14 -176.21(12) . . . . ?
C18 N2 C13 C23 65.18(18) . . . . ?
C19 O7 C18 O6 4.5(3) . . . . ?
C19 O7 C18 N2 -176.43(15) . . . . ?
C23 O9 C24 C25 -86.1(2) . . . . ?
C23 C13 C14 C7 154.29(13) . . . . ?
C24 O9 C23 O8 6.5(3) . . . . ?
C24 O9 C23 C13 -169.77(14) . . . . ?
C24 C25 C26 C27 -178.9(3) . . . . ?
C24 C25 C30 C29 179.0(2) . . . . ?
C25 C26 C27 C28 -0.6(6) . . . . ?
C26 C25 C30 C29 -0.8(4) . . . . ?
C26 C27 C28 C29 0.2(7) . . . . ?
C27 C28 C29 C30 0.0(6) . . . . ?
C28 C29 C30 C25 0.3(5) . . . . ?
C30 C25 C26 C27 0.9(4) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_151201_yk_3_12711
_database_code_depnum_ccdc_archive 'CCDC 1445016'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;
_audit_creation_date             2015-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        C19-epi-ent-3
_chemical_formula_moiety         'C21 H26 N2 O6'
_chemical_formula_sum            'C21 H26 N2 O6'
_chemical_formula_weight         402.44
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 o8 n2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x+1/2, -y, z+1/2'

_cell_length_a                   7.3230(4)
_cell_length_b                   9.7030(6)
_cell_length_c                   13.3813(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.357(6)
_cell_angle_gamma                90.00
_cell_volume                     949.18(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1482
_cell_measurement_temperature    169.6
_cell_measurement_theta_max      29.5429
_cell_measurement_theta_min      3.0437
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3610
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.05
_diffrn_ambient_temperature      169.6
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0704179000
_diffrn_orient_matrix_UB_12      -0.0482102000
_diffrn_orient_matrix_UB_13      0.0080967000
_diffrn_orient_matrix_UB_21      0.0242688000
_diffrn_orient_matrix_UB_22      -0.0377246000
_diffrn_orient_matrix_UB_23      -0.0426668000
_diffrn_orient_matrix_UB_31      0.0622074000
_diffrn_orient_matrix_UB_32      -0.0398867000
_diffrn_orient_matrix_UB_33      0.0305698000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1592
_reflns_number_total             1738
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         1738
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0601P)²+0.0617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0968
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C16(H16), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.2649(3) 0.2068(2) 1.07432(16) 0.0271(5) Uani 1 d . . .
O2 O 0.0352(3) 0.3759(2) 0.66799(15) 0.0264(5) Uani 1 d . . .
H2 H -0.0483 0.4224 0.6385 0.040 Uiso 1 calc . . GR
O3 O 0.3512(3) 0.5333(3) 0.7981(2) 0.0437(7) Uani 1 d . . .
O4 O 0.2409(3) 0.6984(3) 0.69795(18) 0.0321(6) Uani 1 d . . .
O5 O -0.4137(3) 0.8109(2) 1.01726(17) 0.0271(5) Uani 1 d . . .
H5 H -0.4350 0.7498 1.0595 0.041 Uiso 1 calc . . GR
O18 O 0.3213(3) 0.4707(2) 1.04556(18) 0.0292(6) Uani 1 d . . .
N1 N 0.0996(3) 0.4129(3) 0.92821(18) 0.0196(6) Uani 1 d . . .
N2 N -0.2131(3) 0.4689(3) 0.86245(19) 0.0213(6) Uani 1 d . . .
C1 C 0.2543(4) 0.1834(3) 0.9745(2) 0.0213(7) Uani 1 d . . .
C2 C 0.3233(4) 0.0639(3) 0.9318(3) 0.0272(7) Uani 1 d . . .
H2A H 0.3961 0.0024 0.9725 0.033 Uiso 1 calc . . R
C3 C 0.2873(5) 0.0340(3) 0.8314(3) 0.0297(8) Uani 1 d . . .
H3 H 0.3395 -0.0459 0.8036 0.036 Uiso 1 calc . . R
C4 C 0.1770(4) 0.1183(3) 0.7715(2) 0.0272(7) Uani 1 d . . .
H4 H 0.1445 0.0943 0.7039 0.033 Uiso 1 calc . . R
C5 C 0.1150(4) 0.2384(3) 0.8122(2) 0.0225(7) Uani 1 d . . .
C6 C 0.1624(4) 0.2765(3) 0.9101(2) 0.0214(7) Uani 1 d . . .
C7 C -0.0243(4) 0.4596(3) 0.8398(2) 0.0203(7) Uani 1 d . . .
C8 C -0.0188(4) 0.3372(3) 0.7641(2) 0.0214(7) Uani 1 d . . .
C9 C -0.2162(4) 0.2802(4) 0.7622(2) 0.0266(7) Uani 1 d . . .
H9A H -0.2903 0.3158 0.7035 0.032 Uiso 1 calc . . R
H9B H -0.2163 0.1782 0.7598 0.032 Uiso 1 calc . . R
C10 C -0.2902(4) 0.3317(3) 0.8593(2) 0.0246(7) Uani 1 d . . .
H10A H -0.4256 0.3337 0.8558 0.030 Uiso 1 calc . . R
H10B H -0.2452 0.2757 0.9174 0.030 Uiso 1 calc . . R
C11 C -0.2530(4) 0.5608(3) 0.9438(2) 0.0227(7) Uani 1 d . . .
H11A H -0.1895 0.5289 1.0069 0.027 Uiso 1 calc . . R
H11B H -0.3862 0.5620 0.9529 0.027 Uiso 1 calc . . R
C12 C -0.1876(4) 0.7045(3) 0.9178(2) 0.0214(6) Uani 1 d . . .
H12 H -0.2617 0.7338 0.8563 0.026 Uiso 1 calc . . R
C13 C 0.0133(4) 0.7005(3) 0.8897(2) 0.0205(6) Uani 1 d . . .
H13 H 0.0489 0.7945 0.8672 0.025 Uiso 1 calc . . R
C14 C 0.1469(4) 0.6559(3) 0.9770(2) 0.0251(7) Uani 1 d . . .
H14A H 0.2617 0.7086 0.9717 0.030 Uiso 1 calc . . R
H14B H 0.0938 0.6845 1.0401 0.030 Uiso 1 calc . . R
C15 C 0.1963(4) 0.5055(4) 0.9863(2) 0.0216(7) Uani 1 d . . .
C16 C 0.0331(4) 0.5986(3) 0.8026(2) 0.0199(6) Uani 1 d . . .
H16 H -0.0537 0.6266 0.7457 0.024 Uiso 1 calc . . R
C17 C 0.2259(4) 0.6020(3) 0.7670(2) 0.0231(7) Uani 1 d . . .
C18 C 0.4220(5) 0.7145(4) 0.6613(3) 0.0356(8) Uani 1 d . . .
H18A H 0.5060 0.7486 0.7155 0.053 Uiso 1 calc . . GR
H18B H 0.4172 0.7804 0.6058 0.053 Uiso 1 calc . . GR
H18C H 0.4654 0.6252 0.6380 0.053 Uiso 1 calc . . GR
C19 C -0.2237(4) 0.8100(3) 0.9988(3) 0.0271(7) Uani 1 d . . .
H19 H -0.1518 0.7841 1.0618 0.032 Uiso 1 calc . . R
C20 C -0.1744(6) 0.9553(4) 0.9703(4) 0.0508(11) Uani 1 d . . .
H20A H -0.2076 1.0189 1.0231 0.076 Uiso 1 calc . . GR
H20B H -0.2409 0.9802 0.9072 0.076 Uiso 1 calc . . GR
H20C H -0.0425 0.9610 0.9621 0.076 Uiso 1 calc . . GR
C21 C 0.3552(6) 0.1075(4) 1.1363(3) 0.0361(9) Uani 1 d . . .
H21A H 0.3436 0.1322 1.2066 0.054 Uiso 1 calc . . GR
H21B H 0.4849 0.1043 1.1220 0.054 Uiso 1 calc . . GR
H21C H 0.2998 0.0168 1.1232 0.054 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.353(4) . ?
O1 C21 1.410(4) . ?
O2 H2 0.8400 . ?
O2 C8 1.418(4) . ?
O3 C17 1.190(4) . ?
O4 C17 1.324(4) . ?
O4 C18 1.449(4) . ?
O5 H5 0.8400 . ?
O5 C19 1.427(4) . ?
O18 C15 1.223(4) . ?
N1 C6 1.427(4) . ?
N1 C7 1.517(4) . ?
N1 C15 1.359(4) . ?
N2 C7 1.436(4) . ?
N2 C10 1.445(4) . ?
N2 C11 1.450(4) . ?
C1 C2 1.400(5) . ?
C1 C6 1.394(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.385(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(5) . ?
C5 C6 1.386(4) . ?
C5 C8 1.490(4) . ?
C7 C8 1.563(4) . ?
C7 C16 1.506(4) . ?
C8 C9 1.547(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.522(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.521(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.540(4) . ?
C12 C19 1.525(4) . ?
C13 H13 1.0000 . ?
C13 C14 1.540(4) . ?
C13 C16 1.542(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.507(5) . ?
C16 H16 1.0000 . ?
C16 C17 1.516(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.509(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C21 117.6(3) . . ?
C8 O2 H2 109.5 . . ?
C17 O4 C18 115.3(3) . . ?
C19 O5 H5 109.5 . . ?
C6 N1 C7 109.2(2) . . ?
C15 N1 C6 123.2(2) . . ?
C15 N1 C7 121.1(3) . . ?
C7 N2 C10 108.4(2) . . ?
C7 N2 C11 115.9(2) . . ?
C10 N2 C11 119.5(2) . . ?
O1 C1 C2 122.7(3) . . ?
O1 C1 C6 120.0(3) . . ?
C6 C1 C2 117.2(3) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2A 119.4 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 C8 126.8(3) . . ?
C6 C5 C8 111.0(3) . . ?
C1 C6 N1 130.1(3) . . ?
C5 C6 N1 110.1(3) . . ?
C5 C6 C1 119.8(3) . . ?
N1 C7 C8 104.0(2) . . ?
N2 C7 N1 113.2(2) . . ?
N2 C7 C8 104.3(2) . . ?
N2 C7 C16 107.7(2) . . ?
C16 C7 N1 111.1(2) . . ?
C16 C7 C8 116.6(3) . . ?
O2 C8 C5 110.5(3) . . ?
O2 C8 C7 113.9(3) . . ?
O2 C8 C9 113.0(2) . . ?
C5 C8 C7 104.5(2) . . ?
C5 C8 C9 111.6(3) . . ?
C9 C8 C7 102.9(3) . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C8 104.3(2) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
N2 C10 C9 99.7(3) . . ?
N2 C10 H10A 111.8 . . ?
N2 C10 H10B 111.8 . . ?
C9 C10 H10A 111.8 . . ?
C9 C10 H10B 111.8 . . ?
H10A C10 H10B 109.5 . . ?
N2 C11 H11A 110.1 . . ?
N2 C11 H11B 110.1 . . ?
N2 C11 C12 108.2(3) . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
C11 C12 H12 106.6 . . ?
C11 C12 C13 110.5(2) . . ?
C11 C12 C19 112.5(3) . . ?
C13 C12 H12 106.6 . . ?
C19 C12 H12 106.6 . . ?
C19 C12 C13 113.4(2) . . ?
C12 C13 H13 108.7 . . ?
C12 C13 C16 109.5(2) . . ?
C14 C13 C12 113.3(3) . . ?
C14 C13 H13 108.7 . . ?
C14 C13 C16 108.0(2) . . ?
C16 C13 H13 108.7 . . ?
C13 C14 H14A 107.7 . . ?
C13 C14 H14B 107.7 . . ?
H14A C14 H14B 107.1 . . ?
C15 C14 C13 118.3(3) . . ?
C15 C14 H14A 107.7 . . ?
C15 C14 H14B 107.7 . . ?
O18 C15 N1 122.2(3) . . ?
O18 C15 C14 119.2(3) . . ?
N1 C15 C14 118.5(3) . . ?
C7 C16 C13 106.5(2) . . ?
C7 C16 H16 108.5 . . ?
C7 C16 C17 114.0(3) . . ?
C13 C16 H16 108.5 . . ?
C17 C16 C13 110.7(2) . . ?
C17 C16 H16 108.5 . . ?
O3 C17 O4 123.1(3) . . ?
O3 C17 C16 126.2(3) . . ?
O4 C17 C16 110.6(3) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 C12 109.8(3) . . ?
O5 C19 H19 109.0 . . ?
O5 C19 C20 106.8(3) . . ?
C12 C19 H19 109.0 . . ?
C20 C19 C12 113.2(3) . . ?
C20 C19 H19 109.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 170.6(3) . . . . ?
O1 C1 C6 N1 13.1(5) . . . . ?
O1 C1 C6 C5 -165.2(3) . . . . ?
O2 C8 C9 C10 -144.2(3) . . . . ?
N1 C7 C8 O2 -124.5(2) . . . . ?
N1 C7 C8 C5 -3.8(3) . . . . ?
N1 C7 C8 C9 112.9(3) . . . . ?
N1 C7 C16 C13 -61.9(3) . . . . ?
N1 C7 C16 C17 60.5(3) . . . . ?
N2 C7 C8 O2 116.7(3) . . . . ?
N2 C7 C8 C5 -122.5(2) . . . . ?
N2 C7 C8 C9 -5.9(3) . . . . ?
N2 C7 C16 C13 62.6(3) . . . . ?
N2 C7 C16 C17 -175.1(2) . . . . ?
N2 C11 C12 C13 -52.2(3) . . . . ?
N2 C11 C12 C19 179.8(2) . . . . ?
C1 C2 C3 C4 -2.4(5) . . . . ?
C2 C1 C6 N1 -170.6(3) . . . . ?
C2 C1 C6 C5 11.1(4) . . . . ?
C2 C3 C4 C5 4.9(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C3 C4 C5 C8 -173.8(3) . . . . ?
C4 C5 C6 N1 172.3(3) . . . . ?
C4 C5 C6 C1 -9.1(5) . . . . ?
C4 C5 C8 O2 -52.1(4) . . . . ?
C4 C5 C8 C7 -175.1(3) . . . . ?
C4 C5 C8 C9 74.5(4) . . . . ?
C5 C8 C9 C10 90.6(3) . . . . ?
C6 N1 C7 N2 109.4(3) . . . . ?
C6 N1 C7 C8 -3.1(3) . . . . ?
C6 N1 C7 C16 -129.3(3) . . . . ?
C6 N1 C15 O18 -17.6(5) . . . . ?
C6 N1 C15 C14 162.5(3) . . . . ?
C6 C1 C2 C3 -5.6(5) . . . . ?
C6 C5 C8 O2 132.7(3) . . . . ?
C6 C5 C8 C7 9.8(3) . . . . ?
C6 C5 C8 C9 -100.7(3) . . . . ?
C7 N1 C6 C1 -169.0(3) . . . . ?
C7 N1 C6 C5 9.4(3) . . . . ?
C7 N1 C15 O18 -166.1(3) . . . . ?
C7 N1 C15 C14 13.9(4) . . . . ?
C7 N2 C10 C9 -46.0(3) . . . . ?
C7 N2 C11 C12 58.5(3) . . . . ?
C7 C8 C9 C10 -20.9(3) . . . . ?
C7 C16 C17 O3 -30.7(5) . . . . ?
C7 C16 C17 O4 152.2(3) . . . . ?
C8 C5 C6 N1 -12.2(3) . . . . ?
C8 C5 C6 C1 166.4(3) . . . . ?
C8 C7 C16 C13 179.3(2) . . . . ?
C8 C7 C16 C17 -58.4(3) . . . . ?
C8 C9 C10 N2 39.7(3) . . . . ?
C10 N2 C7 N1 -79.3(3) . . . . ?
C10 N2 C7 C8 33.0(3) . . . . ?
C10 N2 C7 C16 157.5(2) . . . . ?
C10 N2 C11 C12 -168.9(2) . . . . ?
C11 N2 C7 N1 58.2(3) . . . . ?
C11 N2 C7 C8 170.5(2) . . . . ?
C11 N2 C7 C16 -65.0(3) . . . . ?
C11 N2 C10 C9 178.3(3) . . . . ?
C11 C12 C13 C14 -64.1(3) . . . . ?
C11 C12 C13 C16 56.5(3) . . . . ?
C11 C12 C19 O5 -55.9(3) . . . . ?
C11 C12 C19 C20 -175.1(3) . . . . ?
C12 C13 C14 C15 93.2(3) . . . . ?
C12 C13 C16 C7 -60.7(3) . . . . ?
C12 C13 C16 C17 174.9(2) . . . . ?
C13 C12 C19 O5 177.6(2) . . . . ?
C13 C12 C19 C20 58.5(4) . . . . ?
C13 C14 C15 O18 169.4(3) . . . . ?
C13 C14 C15 N1 -10.6(4) . . . . ?
C13 C16 C17 O3 89.3(4) . . . . ?
C13 C16 C17 O4 -87.8(3) . . . . ?
C14 C13 C16 C7 63.1(3) . . . . ?
C14 C13 C16 C17 -61.3(3) . . . . ?
C15 N1 C6 C1 39.2(5) . . . . ?
C15 N1 C6 C5 -142.3(3) . . . . ?
C15 N1 C7 N2 -98.1(3) . . . . ?
C15 N1 C7 C8 149.4(3) . . . . ?
C15 N1 C7 C16 23.2(4) . . . . ?
C16 C7 C8 O2 -1.9(4) . . . . ?
C16 C7 C8 C5 118.9(3) . . . . ?
C16 C7 C8 C9 -124.5(3) . . . . ?
C16 C13 C14 C15 -28.3(4) . . . . ?
C18 O4 C17 O3 0.5(5) . . . . ?
C18 O4 C17 C16 177.7(3) . . . . ?
C19 C12 C13 C14 63.3(3) . . . . ?
C19 C12 C13 C16 -176.0(3) . . . . ?
C21 O1 C1 C2 2.2(4) . . . . ?
C21 O1 C1 C6 178.3(3) . . . . ?

